#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/22/1502278.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502278
loop_
_publ_author_name
'Zhang, Gen'
'Zhang, Yaohu'
'Jiang, Xianxing'
'Yan, Wenjin'
'Wang, Rui'
_publ_section_title
;
 Highly enantioslective synthesis of multisubstituted polyfunctional
 dihydropyrrole via an organocatalytic tandem Michael/cyclization
 sequence.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3806
_journal_page_last               3809
_journal_paper_doi               10.1021/ol201299u
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C18 H17 Br N3 O5'
_chemical_formula_weight         435.26
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.50(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.36(3)
_cell_length_b                   14.78(4)
_cell_length_c                   13.66(4)
_cell_measurement_reflns_used    2165
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.42
_cell_measurement_theta_min      2.25
_cell_volume                     2042(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_sigmaI/netI    0.0620
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14340
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    2.046
_exptl_absorpt_correction_T_max  0.6395
_exptl_absorpt_correction_T_min  0.5606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             884
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.580
_refine_diff_density_min         -0.770
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3781
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1381
_refine_ls_R_factor_gt           0.0594
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0364P)²+5.0399P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1545
_reflns_number_gt                1875
_reflns_number_total             3781
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol201299u_si_002.cif
_cod_data_source_block           p21n
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2041(10)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1502278
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.0848(4) 0.7771(3) 0.4592(4) 0.0407(12) Uani 1 1 d .
C2 C 0.1996(4) 0.7825(3) 0.3982(4) 0.0445(12) Uani 1 1 d .
C3 C 0.2772(4) 0.8631(3) 0.4495(4) 0.0416(12) Uani 1 1 d .
C4 C 0.2143(4) 0.9087(3) 0.5125(3) 0.0377(11) Uani 1 1 d .
C5 C -0.0539(5) 0.7651(4) 0.3912(4) 0.0449(13) Uani 1 1 d .
C6 C -0.1903(6) 0.6570(5) 0.2863(5) 0.082(2) Uani 1 1 d .
H6A H -0.1754 0.6094 0.2411 0.098 Uiso 1 1 calc R
H6B H -0.2255 0.7092 0.2463 0.098 Uiso 1 1 calc R
C7 C -0.2868(7) 0.6258(7) 0.3445(6) 0.145(4) Uani 1 1 d .
H7A H -0.2464 0.5809 0.3922 0.218 Uiso 1 1 calc R
H7B H -0.3622 0.5999 0.2997 0.218 Uiso 1 1 calc R
H7C H -0.3146 0.6761 0.3792 0.218 Uiso 1 1 calc R
C8 C 0.1130(6) 0.6965(4) 0.5348(4) 0.0541(14) Uani 1 1 d .
C9 C 0.0408(9) 0.6309(5) 0.6760(6) 0.108(3) Uani 1 1 d .
H9A H 0.1289 0.6050 0.6906 0.130 Uiso 1 1 calc R
H9B H 0.0251 0.6582 0.7370 0.130 Uiso 1 1 calc R
C10 C -0.0567(9) 0.5601(5) 0.6421(6) 0.121(3) Uani 1 1 d .
H10A H -0.1434 0.5863 0.6255 0.181 Uiso 1 1 calc R
H10B H -0.0529 0.5163 0.6945 0.181 Uiso 1 1 calc R
H10C H -0.0378 0.5310 0.5838 0.181 Uiso 1 1 calc R
C11 C 0.1506(5) 0.7964(3) 0.2839(4) 0.0467(13) Uani 1 1 d .
C12 C 0.1714(5) 0.7325(4) 0.2135(5) 0.0645(17) Uani 1 1 d .
C13 C 0.1237(7) 0.7471(6) 0.1105(6) 0.092(2) Uani 1 1 d .
H13 H 0.1405 0.7046 0.0645 0.110 Uiso 1 1 calc R
C14 C 0.0524(7) 0.8234(7) 0.0771(5) 0.098(3) Uani 1 1 d .
H14 H 0.0173 0.8311 0.0089 0.117 Uiso 1 1 calc R
C15 C 0.0326(7) 0.8891(5) 0.1448(5) 0.085(2) Uani 1 1 d .
H15 H -0.0135 0.9417 0.1222 0.102 Uiso 1 1 calc R
C16 C 0.0827(5) 0.8754(4) 0.2471(4) 0.0603(15) Uani 1 1 d .
H16 H 0.0707 0.9201 0.2922 0.072 Uiso 1 1 calc R
C17 C 0.3990(5) 0.8911(3) 0.4295(4) 0.0500(14) Uani 1 1 d .
C18 C 0.0027(5) 0.8922(4) 0.5686(4) 0.0487(13) Uani 1 1 d .
H18 H -0.0722 0.8566 0.5651 0.058 Uiso 1 1 calc R
Br1 Br 0.27013(9) 0.62428(5) 0.25306(7) 0.1100(4) Uani 1 1 d .
N1 N 0.0941(4) 0.8640(2) 0.5159(3) 0.0399(10) Uani 1 1 d .
N2 N 0.5001(5) 0.9122(3) 0.4132(4) 0.0692(14) Uani 1 1 d .
N3 N 0.2491(4) 0.9833(3) 0.5677(3) 0.0486(11) Uani 1 1 d .
H3A H 0.3224 1.0102 0.5665 0.058 Uiso 1 1 calc R
H3B H 0.1982 1.0043 0.6044 0.058 Uiso 1 1 calc R
O1 O -0.1375(3) 0.8230(3) 0.3737(3) 0.0609(10) Uani 1 1 d .
O2 O -0.0637(3) 0.6813(2) 0.3543(3) 0.0600(10) Uani 1 1 d .
O3 O 0.1945(4) 0.6393(3) 0.5357(4) 0.0932(15) Uani 1 1 d .
O4 O 0.0306(5) 0.7006(3) 0.5967(3) 0.0868(14) Uani 1 1 d .
O5 O 0.0127(3) 0.9607(3) 0.6199(3) 0.0588(10) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C1 C5 111.0(4)
N1 C1 C8 109.4(4)
C5 C1 C8 109.1(4)
N1 C1 C2 104.8(4)
C5 C1 C2 113.2(4)
C8 C1 C2 109.3(4)
C3 C2 C11 112.7(4)
C3 C2 C1 100.3(4)
C11 C2 C1 114.5(4)
C4 C3 C17 123.2(5)
C4 C3 C2 113.6(4)
C17 C3 C2 123.1(4)
N3 C4 C3 130.8(4)
N3 C4 N1 119.7(4)
C3 C4 N1 109.4(4)
O1 C5 O2 126.3(5)
O1 C5 C1 125.0(5)
O2 C5 C1 108.6(4)
O2 C6 C7 110.5(6)
O2 C6 H6A 109.6
C7 C6 H6A 109.6
O2 C6 H6B 109.6
C7 C6 H6B 109.6
H6A C6 H6B 108.1
C6 C7 H7A 109.5
C6 C7 H7B 109.5
H7A C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
O3 C8 O4 125.4(6)
O3 C8 C1 125.2(6)
O4 C8 C1 109.4(5)
C10 C9 O4 109.3(6)
C10 C9 H9A 109.8
O4 C9 H9A 109.8
C10 C9 H9B 109.8
O4 C9 H9B 109.8
H9A C9 H9B 108.3
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C12 C11 C16 117.2(5)
C12 C11 C2 122.6(5)
C16 C11 C2 120.1(4)
C11 C12 C13 120.8(6)
C11 C12 Br1 121.6(5)
C13 C12 Br1 117.5(5)
C14 C13 C12 120.5(7)
C14 C13 H13 119.8
C12 C13 H13 119.8
C13 C14 C15 120.1(7)
C13 C14 H14 120.0
C15 C14 H14 120.0
C14 C15 C16 119.3(7)
C14 C15 H15 120.3
C16 C15 H15 120.3
C15 C16 C11 121.9(6)
C15 C16 H16 119.0
C11 C16 H16 119.0
N2 C17 C3 178.6(6)
O5 C18 N1 124.7(5)
O5 C18 H18 117.6
N1 C18 H18 117.6
C18 N1 C4 125.8(4)
C18 N1 C1 124.0(4)
C4 N1 C1 110.0(4)
C4 N3 H3A 120.0
C4 N3 H3B 120.0
H3A N3 H3B 120.0
C5 O2 C6 116.6(5)
C8 O4 C9 118.6(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.492(7)
C1 C5 1.544(8)
C1 C8 1.562(8)
C1 C2 1.595(7)
C2 C3 1.520(7)
C2 C11 1.547(8)
C3 C4 1.365(7)
C3 C17 1.411(8)
C4 N3 1.340(6)
C4 N1 1.419(6)
C5 O1 1.204(6)
C5 O2 1.332(7)
C6 O2 1.478(7)
C6 C7 1.479(10)
C6 H6A 0.9700
C6 H6B 0.9700
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C8 O3 1.193(7)
C8 O4 1.326(7)
C9 C10 1.459(10)
C9 O4 1.483(7)
C9 H9A 0.9700
C9 H9B 0.9700
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C11 C12 1.396(7)
C11 C16 1.399(8)
C12 C13 1.403(10)
C12 Br1 1.912(8)
C13 C14 1.371(11)
C13 H13 0.9300
C14 C15 1.386(10)
C14 H14 0.9300
C15 C16 1.397(9)
C15 H15 0.9300
C16 H16 0.9300
C17 N2 1.160(7)
C18 O5 1.222(6)
C18 N1 1.373(7)
C18 H18 0.9300
N3 H3A 0.8600
N3 H3B 0.8600
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
N1 C1 C2 C3 12.9(5)
C5 C1 C2 C3 133.9(4)
C8 C1 C2 C3 -104.3(5)
N1 C1 C2 C11 -108.1(4)
C5 C1 C2 C11 13.0(6)
C8 C1 C2 C11 134.7(4)
C11 C2 C3 C4 112.2(5)
C1 C2 C3 C4 -10.1(5)
C11 C2 C3 C17 -64.4(6)
C1 C2 C3 C17 173.3(5)
C17 C3 C4 N3 -1.3(8)
C2 C3 C4 N3 -177.9(5)
C17 C3 C4 N1 179.5(4)
C2 C3 C4 N1 2.9(6)
N1 C1 C5 O1 10.6(7)
C8 C1 C5 O1 131.2(6)
C2 C1 C5 O1 -106.9(6)
N1 C1 C5 O2 -170.7(4)
C8 C1 C5 O2 -50.1(5)
C2 C1 C5 O2 71.8(5)
N1 C1 C8 O3 -125.4(6)
C5 C1 C8 O3 113.0(6)
C2 C1 C8 O3 -11.2(7)
N1 C1 C8 O4 55.6(5)
C5 C1 C8 O4 -65.9(6)
C2 C1 C8 O4 169.9(4)
C3 C2 C11 C12 129.4(5)
C1 C2 C11 C12 -116.8(5)
C3 C2 C11 C16 -50.5(6)
C1 C2 C11 C16 63.4(6)
C16 C11 C12 C13 -1.1(8)
C2 C11 C12 C13 179.0(5)
C16 C11 C12 Br1 176.9(4)
C2 C11 C12 Br1 -2.9(7)
C11 C12 C13 C14 -1.8(10)
Br1 C12 C13 C14 -179.9(5)
C12 C13 C14 C15 3.2(11)
C13 C14 C15 C16 -1.8(11)
C14 C15 C16 C11 -1.2(9)
C12 C11 C16 C15 2.6(8)
C2 C11 C16 C15 -177.6(5)
C4 C3 C17 N2 136(22)
C2 C3 C17 N2 -48(23)
O5 C18 N1 C4 0.4(8)
O5 C18 N1 C1 175.7(5)
N3 C4 N1 C18 3.1(7)
C3 C4 N1 C18 -177.6(4)
N3 C4 N1 C1 -172.8(4)
C3 C4 N1 C1 6.5(5)
C5 C1 N1 C18 49.0(6)
C8 C1 N1 C18 -71.4(6)
C2 C1 N1 C18 171.5(4)
C5 C1 N1 C4 -135.0(4)
C8 C1 N1 C4 104.6(4)
C2 C1 N1 C4 -12.5(5)
O1 C5 O2 C6 -0.9(8)
C1 C5 O2 C6 -179.6(4)
C7 C6 O2 C5 -85.5(7)
O3 C8 O4 C9 1.8(9)
C1 C8 O4 C9 -179.3(5)
C10 C9 O4 C8 -97.1(8)
